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Selling insurance? There's a side hustle for that

The side hustle concept, in the minds of two crafty entrepreneurs, can go deeper than service, and surface, level.

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Need extra cash? You could drive for Uber, shop for and deliver groceries for Instacart or schlep packages for Amazon.

Or you could sell insurance. Or even human resource outsourcing plans.

Welcome to the gig economy, 2.0.

Beyond the obvious side hustles in cars and shopping carts, two separate area entrepreneurs, unconnected, recently launched ventures that connect like-minded gig economy players with extra cash opportunities. One, from Clearwater-based Strategic Insurance Services owner Doug Levi, is in insurance sales. The other is Lakewood Ranch-based Advantage Business Partners, founded by Sarasota-Bradenton area Professional Employer Organization Executive Carlos Cardenas. 

“This is great for people who want to add some residual income or who want to start their own business but don’t have the capital to do it right now,” Cardenas says, speaking about his startup, ABP, which has other revenue streams besides side hustles and all attempts to capitalize on the gig economy. ABP has a consultant-like, side hustle system, where people who are in front of business owners can connect them with ABP, which will in turn connect them to the right PEO, for a fee. “People are looking for more freedom and more opportunities to own their own business.”

Levi likewise has high hopes for his gig economy gig, detailed at It starts with a web-based application. The firm then provides training and licensure based on what state users work in. 

‘I started with a philosophy that if I can make the phone ring, I knew I could take care of clients. Then I will figure everything else out.’ Doug Levi, Strategic Insurance Services

Side hustlers through SIS pay $60 for a background check, a one-time marketing fee of $79 and a $59 monthly support fee. Levi, 40, says he doesn’t make money of the background check, and the other payments are both a token for his time and gives the side entrants “skin in the game.”

Support includes what Levi calls a “crash course in insurance” and a 10:30 a.m. video call every Monday to go over prospects. There’s also a closed Facebook support group.

Side hustlers start off selling home and auto insurance and can be trained and certified in other lines, such as commercial, life and health insurance. And they can do it wherever (they are licensed) and whenever they choose — part of Levi’s pitch. They can sell to neighbors, friends, people on line at the Publix deli counter. “It can be done on nights; it can be done on weekends,” Levi says.

An SIS side hustler earns a 50% commission on new clients and 25% on annual renewals. The monthly average income, according to SIS’s side hustle website, ranges from $1,250 to $8,508, though Levi points out payout is relative to what a side hustler puts in. “I tell everyone who signs up I’m responsible to you, not for you,” Levi says.

SIS side hustlers can grow revenue lines faster by participating in direct-selling, or multilevel marketing, by adding other side hustlers to their network. Levi says that’s not a requirement and adds that “for some, direct sales has a stigma to it.”

Levi founded SIS in 2006 — when he was 26 years old — after relocating to the Clearwater area from suburban Philadelphia. The firm now does work in 12 states, with 22 employee, more than 300 clients and $11.5 million in premiums. “I started with a philosophy that if I can make the phone ring, I knew I could take care of clients,” says Levi, who previously worked for State Farm. “Then I will figure everything else out.”

SIS has since had posted steady growth, but Levi believes his side hustle venture is his next best, and biggest, thing. Although selling insurance on the side isn’t totally new — Primerica, now a multibillion-dollar firm, pioneered part-time life insurance sales in 1977 — Levi believes he’s enhanced it like never before. “I’ve always liked that concept,” Levi says.

Mark Wemple. Doug Levi has high hopes for his side venture, which allows people to sell insurance as a side hustle.
Mark Wemple. Doug Levi has high hopes for his side venture, which allows people to sell insurance as a side hustle.

The platform debuted in January, and 14 people have signed on, from a teacher to a CrossFit gym owner, and as far away as Arizona. Another 30-40 a month have expressed interest, Levi says. He aims to sign up 100 people next year, a few hundred in 2021 and hit 1,000 in five years. He’s working on a limited marketing budget, leaning, so far, on Facebook and Indeed ads and word of mouth.

“I think we are coming to a point in this industry where we have to start doing things differently,” Levi says. “The sky's the limit with this.”


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